(+/-)-stemodin

Base Information

• Chemical Name: (+/-)-stemodin
• CAS No.: 76739-56-5
• Molecular Formula: C₂₀H₃₄O₂
• Molecular Weight: 306.489
• Mol file: 76739-56-5.mol

Synonyms:

Chemical Property of (+/-)-stemodin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-stemodin

There total 50 articles about (+/-)-stemodin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(+/-)-stemodinone (41943-80-0,76739-57-6) → (+/-)-stemodin (41943-79-7,76739-56-5)

Guidance literature:

With ethanol; sodium; In tetrahydrofuran; at 0 ℃; Yield given;

DOI:10.1021/ja00545a060

Reference yield:

(+/-)-stemod-2-en-13α-ol (76685-64-8,76739-59-8) → (+/-)-stemodin (41943-79-7,76739-56-5)

Guidance literature:

With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide; Yield given. Multistep reaction; 1.) THF, reflux, 48 h, 2.) THF/ethanol, 50 deg C, 1 h;

DOI:10.1139/v85-563

Reference yield:

(4aS,8aS)-5,5,8a-Trimethyl-2-oxo-1,2,3,4,4a,5,8,8a-octahydro-naphthalene-1-carbaldehyde (76685-50-2) → C20H34O2 (41943-79-7,76739-56-5)

Guidance literature:

Multi-step reaction with 16 steps

1: 70 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene, potassium carbonate / tetrahydrofuran; 2-methyl-propan-2-ol / 23 °C

2: 93 percent / pyrrolidinium acetate / tetrahydrofuran; methanol / 23 °C

3: zinc iodide / CHCl₃ / 23 °C

4: 87 percent

5: 80 percent / diisobutylaluminum hydride / toluene / -10 - -5 °C

6: 1.) trimethylsilyllithium, 2.) lithium diisopropylamide / 1.) ether, HMPA, -35 deg C, 2.) THF, HMPA, 23 deg C

7: sodium borohydride / tetrahydrofuran; ethanol / 0 °C

8: 4-(dimethylamino)pyridine / pyridine; CHCl₃ / 23 °C

9: 1,3-diiodo-5,5-dimethylhydantoin / acetone; tetrahydrofuran; H₂O / 0.5 h / -20 °C

10: potassium tert-butoxide / tetrahydrofuran / 23 °C

11: lithium, liquid ammonia / -78 °C

12: diethyl ether / 0 °C

13: N-bromoacetamide / acetone; H₂O

14: PCC / CH₂Cl₂

15: 80 percent / zinc, aq. ammonium chloride / diethyl ether / 23 °C

16: sodium borohydride

With trimethylsilyl lithium; dmap; sodium tetrahydroborate; 1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione; ammonium chloride; potassium tert-butylate; ammonia; lithium; diisobutylaluminium hydride; pyrrolidine acetic acid; potassium carbonate; pyridinium chlorochromate; zinc(II) iodide; 1,5-Diazabicyclo[5.4.0]undec-5-ene; zinc; lithium diisopropyl amide; N-bromoacetamide; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; chloroform; water; acetone; toluene; tert-butyl alcohol;

DOI:10.1021/ja00545a060

upstream raw materials:

(+/-)-stemodinone

(4aS,8aS)-5,5,8a-Trimethyl-2-oxo-1,2,3,4,4a,5,8,8a-octahydro-naphthalene-1-carbaldehyde

C₁₉H₂₈O

((4'aR,8'aR)-5',5',8'a-Trimethyl-3',4',4'a,5',8',8'a-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-1'-yl)-methanol